It’s like so blah, right?
Sky’s family goes on the same vacation every year to the beautiful Lanai Beach Resort + Spa in sunny sunny Fort Lauderdale, Florida. It’s always his dad’s birthday gift to him, kind of – they’d be going on a family vacation anyway, but his birthday always coincides with the first day of the trip and he just combines them all to get away with not getting any other present. Sky isn’t ungrateful – he knows that not everyone gets to go on a nice vacation every year and it really is a gift just to get to go – but he’s gone here for 18 years straight. He’s 18 as of the start of the trip and heading off to college at the end of the summer, so he’d like a little more adventure beyond playing badminton with the other guys his age and drinking virgin pina coladas on the beach.
So yeah. Blah.
Thankfully his parents give him a little more agency than they did a few years ago. Him and his younger brother Ace are old enough that they don’t need to be supervised, and his parents are close enough to being empty nesters that they just want to find a beach chair by the pool and read their books. After family breakfast, it’s free reign until dinner.
He’s settled into a routine. They checked in at 3 the first day and had birthday dinner as family, complete with the waiters bringing a cake in with an 18 candle on top, everyone singing happy birthday. and Sky putting his head in his paw in embarrassment. The next two days were exactly the same – put his bathing suit on in the morning, go for a swim, watch Youtube Shorts by the ocean, lunch, a little badminton, a little snorkeling, hang out in the hotel room, dinner, watch the waves, talk to his brother in their bedroom for a while, go to sleep.
The plan for today is exactly the same, actually. On a beach chair by the pool, he pulls his phone out. He starts scrolling a little bit, absentmindedly thinking about how hard it is to get off here. He’s never quite found a way to get everyone off of his tail long enough for him to bust one out.
Then he realizes – he’s 18 years old now. He could totally download one of those hookup apps and find someone here to have sex with. His heart starts racing as he downloads one and fills out the profile. He’s always wanted to do this, Sky figures, no reason to wait until college.
He keeps the profile vague and puts no photos just in case, only his age and that he’s a bottom. He shops around the app. A few faceless profiles, but those are probably people that live in the surrounding town. He refreshes the app until a new face comes up.
His name is Vic. He’s an attractive older lion with graying fur and a kind smile, maybe 40 or so. The first photo is him in business attire, the second him in a cute green Speedo. He’s looking for a bottom. His bio says he’s currently staying at the Lanai Beach Resort + Spa for a business conference, that he’s married and in an open relationship. And the kicker – his profile says he’s zero feet away.
Sky glances around, trying to stay covert. Vic could literally be anywhere. His parents could literally be anywhere, for that matter. He covers the boner in his beach shorts with a towel and takes a sip of his pina colada like he’s just looking up at the clouds.
And then he realizes what zero feet means. Vic is literally a few deck chairs over, nobody in between them. He’s in a pink Speedo, such a built guy he’s practically bursting out of it. His eyes are closed and he’s bathing in the sun, listening to music in his headphones.
Sky doesn’t hesitate to send a message:
Hey there
He watches Vic out of the corner of his eyes. He must have his notifications on because he checks his phone soon after and sends a quick response:
Hey bud!
You’re super close
Are you staying at Lanai?
SKY:
Yup
VIC:
Got any pics?
Sky sends a few photos over. Nothing too flattering, just dumb photos of him and his buddies and a few selfies. He sees Vic grin and sinks further into his deck chair. This might actually happen.
VIC:
Oh wow
You are such a cutie
SKY:
Thank you hehe
VIC:
Are you looking to have any fun? My room is free :)
SKY:
That sounds really nice
VIC:
Ur super close
You must be right near me
SKY:
I’m actually over here lol
Vic looks up at him and gives the same smile from the photo and a little wave.
Sky gathers his towel and his bag and heads over to the chair right next to him. His legs feel weak as he walks over but he knows he wants this. How could he not with that smile? With those pecs?
“Hey, kid!” Vic says as he sits down. “I didn’t realize you were right there. That’s so funny.”
“Like right there. I’m Sky.”
“Sky, huh? You’re a real cutie.” He reaches forward and puts his paw on Sky’s arm. Sky knows he’s bright red and shaking a little bit. “You like that, huh?”
“Sorry, I’ve just never really… done this before.”
“I mean, no better day, huh? Beautiful beach, lovely sky, free room. We don’t have to do anything you don’t want to.”
“Ummm… I’m just trying to keep this, like, under wraps.”
“Oh oh, sure.” Vic sits up and grabs his bag. “Hey, I’m gonna go back to my room. 314. Probably gonna shower the sun off…” He grins, practically giving him a big wink. “So yeah. 314. I’ll probably be out of the shower in 10 minutes.”
“Okay. I’ll be sunbathing.”
“Alright, kid.” He stands up and walks off, his butt shaking in his pink Speedo. “314.”
Sky sits there and shakes in excitement. He’s never done this before, especially with a sexy older guy. It’s a good thing Vic understood what he was putting down and went off to his room first, because Ace wanders over from the poolside bar soon after. “Hey, bro,” he says, sitting down in the deck chair next to him, the same one Vic was on.
“Hey, man.”
“Who was that?”
“Hm?”
“The lion in the little bitty pink Speedo?”
“Oh, I dunno. Just some guy.”
“What were you talking about?”
“He was like, ‘Oh isn’t the sky so pretty?’” Not untrue. “The kind of thing people say to you on vacation.”
“Bro, people love saying shit like that. This lady asked me which sandals she should buy when I was getting chips earlier. Like, I don’t know, bro. Why am I being roped into this?”
Sky chuckles, but he’s a little too distracted for it to sound completely sincere. “I’m gonna take a walk, I think.”
“Cool. I’m gonna try to get Dad to buy me alcohol,” he says. “Wait, you can buy me alcohol!”
“Oh, wow, um…” Sky stands up, still half-hard. “Okay, I’ll buy us some drinks later around sunset and we can swim. That sound okay?”
“Hell yeah. Have a good walk.”
“Thanks.”
Sky stands at the patio of 314. It’s a really nice room that leads basically straight onto the ocean. He knows deep inside his body this is what he wants – he wouldn’t still be hard if that was the case – but the idea of going in there and hooking up with a guy twice his age still makes him freeze. He takes a deep breath and knocks on the door.
“Come in!” Vic says.
He invites himself in. The air conditioning hits him like a truck. Vic is laying on his bed in a fluffy white bathrobe, watching TV. “Hi.”
“Hey, kid!” Sky shuts the door behind him quickly and steps in. He catches a glimpse of himself in the mirror standing there in his bathing suit, the fur on his chest all scruffy. Right in front of that is the big hulking lion he’s about to have sex with. “You wanna come cuddle?”
“Is that okay?”
He laughs and opens his arm. “Come over here.”
Sky climbs right next to him and Vic pulls him in tight. He’s so warm. Sky doesn’t expect it, but he finds himself wrapping his own arm right over Vic’s body. Somehow, cuddling a man he’s never met before feels so secure. “What are we watching?”
“King crab fishing show.”
“They’re really catching those crabs.”
Vic chuckles and Sky can feel it through his whole body. He smiles. “You’re so handsome.”
Sky tucks his face further in so the lion can’t see him blushing. “Thank you.”
“So gorgeous. I wish I looked half as handsome as you when I was your age.”
It’s quiet for a little bit as they both pretend to watch TV. Sky nuzzles his head in a little more and he can feel Vic smile.
“You’re here with your family, I assume?”
“That’s kind of why I wanted to keep it hush.”
He smiles. “Don’t worry. This stays between us.”
“Thank you.”
“So, uh, when you said you haven’t done this before – you mean with an older man?”
“No, uh…”
“Like hooking up?”
“No.”
“Oh… so you’re a virgin.”
Sky smiles bashfully. “Is that okay?”
Vic sits up and puts a serious expression on his face. “That’s okay, but… are you sure you want your first time to be like this? I don’t mind at all, because, as I said, you’re very cute and I wouldn’t mind taking it slow, but you’re a handsome young man and there are going to be a lot more opportunities to do this for you. And it might be more special then, you get what I’m saying?”
“Well… I dunno. I just turned 18 and I wanted to, you know. Celebrate.”
“How long ago?”
“Three days.”
Vic grins a little. “Oh, wow. Happy birthday.”
“Thank you.”
“What am I talking about, that’s very special.” He chuckles. “Here. Why don’t we have some fun, then I’ll get us something nice from room service. Free of charge.”
“That’s very nice of you.”
“Company credit card!” he laughs, pulling Sky in closer. “What do you want to do?”
He scratches the back of his head. “I didn’t, uh, think I’d get this far.”
Vic grins. “I have an idea.”
“Yeah?”
He shakes his bathrobe open. Up top, his beautiful pecs are exposed. Down lower is his erect cock. “How ‘bout we start here?”
Vic likes the little dog at his feet.
He doesn’t normally do stuff like this. He’s happily married to his husband Greg of ten years now. They both agreed that the other was free to do hookups, especially on something like this like a business trip where they would be away from each other. Vic’s never taken Greg up on that offer until now.
Sure, a week relaxing on the beach (really a week in the boardroom with a few hours here and there on the beach) is nice, but he can feel how much he misses his husband in his aching heart and his aching balls. He’s masturbated a few times now. It was nice to wake up and jerk off like he did when he was in college, but it’s only nice to do that a few times. After a few days of that, he felt so strongly the desire to be with his husband. Since that wasn’t an option, and since they had their deal…
The guy he found on the app is really cute. His name is Sky. Isn’t that nice? Like the blue sky above the ocean? He’s adorable in his little beach shorts. He was so humble in real life, so small and pretty and charming.
When they first got back to the room, Vic was a little hesitant that he might be a little too inexperienced. The kid is three days older than 18 and these are experiences he might want to be having organically with someone his own age. It’s not like that isn’t appealing to Vic, though, and it’s not like he wasn’t doing exactly this when he was 18. The kid has beautiful scruff on his tummy, a cute erection in his beach shorts, and a bashful smile. What else could he want?
Sky climbs to the end of the bed and kneels in front of Vic’s body. He’s staring at it like a deer in headlights, but it’s definitely a lot to take in. Vic is half a foot taller than him and built from years of working out and Sky’s just a scrawny kid.
Sky puts a paw on Vic’s erection and Vic feels the warmth of his touch. He gives it a nice squeeze, then he starts lightly stroking his dick. It’s an odd sensation – Vic’s touched himself the same way every time since he first masturbated and he and Gregg have long since settled into a familiar rhythm. It feels great, no doubt, just different.
Vic grins a little and lays back down. “Just like that. Keep going.”
The boy responds well to praise, he’s learning. He sees the way Sky tries to hide the little smile on his face, the way he scratches the fur on his cheek. Vic moves the fabric of the bathrobe aside and gives the dog full access to all of his good parts – his tail, his thighs, his cock. Sky smushes his face down onto Vic’s thigh and gets into the handjob, his attention not breaking from the big cock in front of him.
“You’re such a good boy,” Vic says after they get comfortable and it starts feeling really good, the type of pleasure you feel deep in your thighs. “You’re doing so good. You like that big cock?”
“I do.”
He grins. It’s so cute that Sky is responding to his sexy talk. “Have you ever seen another man’s cock before?”
“No.”
“Do you like it?”
He blushes so hard. “I do.”
Vic chuckles. “God. I was doing this at your age, kid. No apps back then. You had to go to a public bathroom and pick up on other guys’ signals. I’m sure you could still do that now, but, ah…” He ruffles Sky’s fur. “You’re a good good boy.”
“Can I try…” he whimpers.
“Yeah?”
“Can I try putting it in my mouth?”
“Please, Sky.”
That’s a whole nother battle for Sky, clearly. He pulls away and gives Vic’s cock the same confused expression as before.
“You wanna give it a kiss first?”
“Yeah,” he whispers. “Yeah.”
He goes right in and gives Vic’s cock a kiss where his balls meet his shaft. Vic puts his hands behind his head and lets out a sigh of relaxation. That’s how good his vacation’s going – cute little dogs are kissing his balls. How could it be any better?
Sky quickly figures it out, kissing up the shaft until he reaches the tip of Vic’s dick. There’s a little bit of precum leaking out of the tip that touches Sky’s nose. His kisses turn into little licks of the head of his dick. He has to quickly redirect Sky to not jostle his foreskin too much, but once he gets that down he does it perfectly. He puts his warm mouth around Vic’s dick and pushes down.
“Good boy,” he moans. “You’re learning so quickly.”
Sky puts a paw around the base of Vic’s cock and uses that as a guide, not going any further than where his paw begins. No deepthroating needs to happen because just the few inches he’s sucking feels more than good. He gives Sky a quick warning about his teeth and he quickly corrects. The thought that this kid is going to have a lot of fun in his 20s goes through Vic’s head and he smiles at that.
Sky sucks his dick for about an hour. It’s not like Vic’s counting, but he closes his eyes in pleasure and when he opens them back up, the back of the bed is coated in sweat despite the air conditioning and the sunset is streaming through the window. He does it like it’s the most entertaining thing in the world, like it’s an 1000-piece puzzle, which it just might be to an 18-year-old kid. By the time he comes up an hour later, it seems like there’s no more spit left in his mouth.
“Do you want some water, beautiful?”
Sky nods. “Is that okay?”
“Yeah! Please. Ask for anything you need. Here. Relax. You’ve done such good work so far.”
He lays back in the bed while Vic gets up. Vic finally sloughs the bathrobe off of his body, which he’s sure gives Sky a great view of his butt. His erection shifts from side to side as he walks over. Vic bends down and grabs one of the nice water bottles out of the minifridge. The company credit card’s paying for that anyway. “You can also have any of these snacks if you want, Sky, or I can take you out to dinner if you want.” Vic turns around. “Although I know…”
And he’s surprised. By just how small he is. How cute he is. How lovely the little dog in front of him is. He’s still in his beach shorts after all of this time, his erection still pushing at the fabric. He has a modest expression on his face, a little smile he’s trying to hide. He’s getting lost in the bedsheets.
“You alright, bud?”
“You’re just… really pretty.”
Vic smiles. “Thank you! You’re pretty cute yourself.” He sits next to him and gives him the bottle. “Drink up.”
He holds it with both paws. Vic puts my arm around him and brings him in closer. He wants to protect him. He knows that’s a funny thing to say about a kid he just met, but he feels so much compassion and love towards him. He’s just a little dog exploring himself, just like Vic did when he was his age.
The lion scratches the back of his neck. He downs half the bottle. “Woah. You were really thirsty.”
“I didn’t realize it until I came up and then I was like. Shit.”
“It does that to you. You get transfixed.”
He smiles. “Thank you for being so nice.”
“What? A cute little dog gives me head and I’m mean about it? C’mon.”
“But it’s just an app and it’s just a hookup. But you’re being so nice.”
“I see a lot of you in me. I said that before.”
“What were you doing?”
“Well… this was 1999 in the Northeast. There were definitely gay guys around, but you had to be really careful, especially if it was casual sex like this. And I’d, you know. Jerk off with guys. Suck their dicks. I did it with a police officer once, if you’d believe it. I totally thought he was about to arrest me but he just wanted to get off too, I guess.”
“Woah.” He stares down at the bed and thinks about that for a little bit. “And you’re, like, a cool older guy.”
“I’m 42!”
“Sorry–”
“No no, I’m kidding. College guys seem old at your age. I get it.”
He smiles and nuzzles himself into my arm. “Thank you.”
“Do you wanna keep going? We don’t have to.”
“Can we?”
“Sure! We can just jerk off if you want. Just touch ourselves and cuddle. Does that sound good?”
“It does.”
And so that’s what they do. Sky shimmies his swimsuit off. His cock flops out and hits his belly. It’s a nice cock, average sized and really beautiful. Sky seems a little embarrassed about it, so Vic says nothing and just gives him a big smile and a kiss on the forehead. The lion and the dog stroke themselves together, Sky buried in Vic’s arms.
Orgasm comes quickly for the both of them, but even sooner for Sky than either of them expect. He’s whimpering and cumming all over his tummy after only a few minutes. That’s what an hour of sucking cock will do to you. Vic joins him and lets his load out all over Sky’s tummy too. It feels so great after so long of missing his husband.
They lie together for a little bit. Sky wraps his arms around Vic and hugs him tight. Vic scratches his back.
And just when Vic is about to get up, about to ask about how school is going and suggest they get dinner together, he notices the little dog is asleep in his arms.
“You’ve had a big day, boy,” he whispers to the sleeping dog.
Vic knows this is going to end soon, that Sky’s going to have to get back to his family and Vic’s business trip is going to end and they won’t be here anymore. So he decides to protect the little dog. He doesn’t wake him up. He lets him sleep in his big arms. There will be time for the real world later. For now, they can just cuddle and nap.